BR112012026752A2 - process for the preparation of pyrazole carboxylic acid amides - Google Patents
process for the preparation of pyrazole carboxylic acid amidesInfo
- Publication number
- BR112012026752A2 BR112012026752A2 BR112012026752A BR112012026752A BR112012026752A2 BR 112012026752 A2 BR112012026752 A2 BR 112012026752A2 BR 112012026752 A BR112012026752 A BR 112012026752A BR 112012026752 A BR112012026752 A BR 112012026752A BR 112012026752 A2 BR112012026752 A2 BR 112012026752A2
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- compound
- preparation
- reacting
- bromine
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical class NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- 229910052794 bromium Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Substances 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical group C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
processo para a preparação de amidas do ácido pirazol carboxílico. a presente invenção refere-se a um processo para a preparação da fórmula (i) em que esse processo compreende a) fazer reagir um composto de fórmula (ii) em que x é cloro ou bromo, com uma espécie organometálica, para formar (iii) em que x é cloro ou bromo; fazer reagir a halobenzina com um fulveno (iv); (iv), para formar um composto de fórmula (v); (v), em que x é cloro ou bromo; b) hidrogenar (v), na presença de um catalisador metálico adequado, para formar um composto de fórmula (vi) em que x é cloro ou bromo; e um de entre c1) fazer reagir o composto de fórmula (vi) com nh~3~na presença de um catalisador compreendendo paládio e pelo menos um ligante, para formar o composto de fórmula (vii) d) fazer reagir o composto de fórmula (vii) na presença de uma base, com um composto de fórmula (viii); (viii), para formar o composto de fórmula (i); ou c2) fazer reagir o composto de fórmula (vi), na presença de um catalisador de cobre e um ligante, com o composto de fórmula (viiia); (viiia), para formar o composto de fórmula (i).process for the preparation of pyrazole carboxylic acid amides. The present invention relates to a process for the preparation of formula (I) wherein said process comprises a) reacting a compound of formula (ii) wherein x is chlorine or bromine with an organometallic species to form (iii). ) wherein x is chlorine or bromine; reacting halobenzine with a fulveno (iv); (iv) to form a compound of formula (v); (v) wherein x is chlorine or bromine; b) hydrogenate (v), in the presence of a suitable metal catalyst, to form a compound of formula (vi) wherein x is chlorine or bromine; and one of c1) reacting the compound of formula (vi) with nh -3 in the presence of a catalyst comprising palladium and at least one binder to form the compound of formula (vii) d) reacting the compound of formula (vii) in the presence of a base with a compound of formula (viii); (viii) to form the compound of formula (i); or c2) reacting the compound of formula (vi) in the presence of a copper catalyst and a binder with the compound of formula (vii); (viiia) to form the compound of formula (i).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10160437.9 | 2010-04-20 | ||
| EP10160437 | 2010-04-20 | ||
| PCT/EP2011/055872 WO2011131546A1 (en) | 2010-04-20 | 2011-04-14 | Process for the preparation of pyrazole carboxylic acid amides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012026752A2 true BR112012026752A2 (en) | 2015-09-15 |
| BR112012026752B1 BR112012026752B1 (en) | 2018-02-06 |
Family
ID=44070080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012026752-3A BR112012026752B1 (en) | 2010-04-20 | 2011-04-14 | PROCESS FOR THE PREPARATION OF CARBOXYLIC ACID MEASURES AND SO INTERMEDIATE COMPOUNDS OBTAINED |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8519151B2 (en) |
| EP (1) | EP2560958B1 (en) |
| JP (1) | JP5684897B2 (en) |
| CN (1) | CN102844306B (en) |
| AR (1) | AR080921A1 (en) |
| BR (1) | BR112012026752B1 (en) |
| ES (1) | ES2453919T3 (en) |
| IL (1) | IL222401A (en) |
| MX (1) | MX2012012004A (en) |
| TW (1) | TWI428324B (en) |
| UY (1) | UY33339A (en) |
| WO (1) | WO2011131546A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011131544A1 (en) * | 2010-04-20 | 2011-10-27 | Syngenta Participations Ag | Process for the preparation of pyrazole carboxylic acid amides |
| EP2433922A1 (en) * | 2010-08-25 | 2012-03-28 | Syngenta Participations AG | Process for the preparation of dichlorofulvene |
| TWI534126B (en) | 2011-01-25 | 2016-05-21 | 先正達合夥公司 | Process for the preparation of pyrazole carboxylic acid amides |
| CN103483407B (en) * | 2013-10-10 | 2015-11-18 | 宁夏启元药业有限公司 | A kind of Matachrom extractive crystallization double solvent and extractive crystallization method |
| GB201403438D0 (en) | 2014-02-27 | 2014-04-16 | Syngenta Participations Ag | Polymorphs |
| CN111138364A (en) * | 2018-11-01 | 2020-05-12 | 东莞市东阳光菌阳氢专利农药有限公司 | Preparation method of fluorobenzene ether amide |
| WO2024017788A1 (en) | 2022-07-22 | 2024-01-25 | Syngenta Crop Protection Ag | Solid form of a heterocyclic amide derivative |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH075487B2 (en) | 1985-11-14 | 1995-01-25 | 住友化学工業株式会社 | Method for producing 1-bromo-2-chloro-4-fluorobenzene |
| US5093347A (en) | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
| US7223879B2 (en) | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| DE602006018506D1 (en) * | 2005-10-25 | 2011-01-05 | Syngenta Participations Ag | HETEROCYCLIC AMID DERIVATIVES SUITABLE AS MICROBIOZIDE |
| WO2007124907A2 (en) * | 2006-04-27 | 2007-11-08 | Syngenta Participations Ag | Heterocyclyl-carboxylic acid (benzonorbornene-5-yl)amide derivatives as fungicides for agrochemical use |
| WO2007129736A1 (en) * | 2006-05-10 | 2007-11-15 | Idemitsu Kosan Co., Ltd. | Process for production of dicyclopentadiene |
| MX2009003979A (en) | 2006-10-25 | 2009-04-27 | Syngenta Ltd | Process for the production of substituted bromobenzenes. |
| MY150841A (en) * | 2008-10-27 | 2014-02-28 | Syngenta Participations Ag | Process for the preparation of benzonorbornenes |
| BRPI0923401B1 (en) * | 2008-12-24 | 2021-11-23 | Syngenta Limited | METHOD FOR THE PREPARATION OF ARIL AMIDES AND COMPOUND |
-
2011
- 2011-04-14 CN CN201180019767.3A patent/CN102844306B/en active Active
- 2011-04-14 BR BR112012026752-3A patent/BR112012026752B1/en active IP Right Grant
- 2011-04-14 MX MX2012012004A patent/MX2012012004A/en active IP Right Grant
- 2011-04-14 US US13/642,393 patent/US8519151B2/en active Active
- 2011-04-14 WO PCT/EP2011/055872 patent/WO2011131546A1/en active Application Filing
- 2011-04-14 JP JP2013505410A patent/JP5684897B2/en active Active
- 2011-04-14 ES ES11714296.8T patent/ES2453919T3/en active Active
- 2011-04-14 EP EP11714296.8A patent/EP2560958B1/en active Active
- 2011-04-15 UY UY0001033339A patent/UY33339A/en active IP Right Grant
- 2011-04-18 AR ARP110101325A patent/AR080921A1/en active IP Right Grant
- 2011-04-19 TW TW100113505A patent/TWI428324B/en active
-
2012
- 2012-10-11 IL IL222401A patent/IL222401A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP5684897B2 (en) | 2015-03-18 |
| BR112012026752B1 (en) | 2018-02-06 |
| TW201204703A (en) | 2012-02-01 |
| UY33339A (en) | 2011-12-01 |
| JP2013527841A (en) | 2013-07-04 |
| MX2012012004A (en) | 2012-12-17 |
| EP2560958B1 (en) | 2014-01-01 |
| CN102844306B (en) | 2015-01-14 |
| US20130035495A1 (en) | 2013-02-07 |
| IL222401A (en) | 2015-04-30 |
| ES2453919T3 (en) | 2014-04-08 |
| AR080921A1 (en) | 2012-05-16 |
| CN102844306A (en) | 2012-12-26 |
| EP2560958A1 (en) | 2013-02-27 |
| TWI428324B (en) | 2014-03-01 |
| US8519151B2 (en) | 2013-08-27 |
| WO2011131546A1 (en) | 2011-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B16A | Patent or certificate of addition of invention granted [chapter 16.1 patent gazette] |